Water → HCID 69411785, compound

HRID 2187277Notes

Reaction equation

HRID 2187277 reaction equation
C1(C)C(S(O[CH2:11][CH2:12][CH2:13][C@H:14]([C@@H:16]2[C@:33]3([CH3:34])[C:19]([C:20]4[CH2:21][CH2:22][C@@H:23]5[C@:28]([C:30]=4[CH2:31][CH2:32]3)([CH3:29])[CH2:27][CH2:26][CH:25]([OH:35])[C:24]5([CH3:37])[CH3:36])=[CH:18][CH2:17]2)[CH3:15])(=O)=O)=CC=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[CH3:36][C:24]1([CH3:37])[C@@H:25]([OH:35])[CH2:26][CH2:27][C@@:28]2([CH3:29])[CH:23]1[CH2:22][CH2:21][C:20]1[C:19]3[C@@:33]([CH2:32][CH2:31][C:30]=12)([CH3:34])[C@@H:16]([C@H:14]([CH3:15])[CH2:13][CH2:12][CH3:11])[CH2:17][CH:18]=3

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 86583584HCID 86583584, compound

Product 1

HCID 69411785HCID 69411785, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 24-toluenesulphonyloxy-4,4-dimethyl-5α-chola-8,14-diene-3-ol (100 mg, 0.18 mmol) in diethyl ether (25 mL) was added lithium aluminium hydride (40 mg, 1.1 mmol) and the reaction was stirred 16 hours at room temperature. The reaction was then poured into water and extracted with diethyl ether. Drying over magnesium sulphate, concentration under reduced pressure and purification by flash chromatography gave the title compound (41 mg).

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialDrying over magnesium sulphate, concentration under reduced pressure and purification by flash chromatography

Sources & evidence

ORD record
ord-68aedb1b35344ee4810c2e19e4155814
Source dataset
uspto-grants-2002_06
Patent number
US06407086B2

Reaction notes

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